• Bulletin of the Korean Chemical Society
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• v.27 no.12
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• pp.2023-2027
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• 2006

Dibenzyl sulfide was oxidized at the a-carbon to yield benzaldehyde in the presence of $Pd(NO_3)_2$. Oxygen itself could not oxidize the sulfide directly, instead the nitrato ligand of the palladium complex transferred oxygen to dibenzyl sulfide to form benzaldehyde. The X-ray crystal structure of the intermediate complex, cis-[$Pd(NO_3)_2${$S(CH_2C_6H_5)_2$}$_2$], revealed that the nitrato ligand was unidentate. Para-substituted dibenzyl sulfides I, $(YC_6H_4CH_2)_2S $wherein Y = $OCH_3$, $CH_3$, Cl, CN, or $NO_2$, were synthesized and reacted with palladium nitrate, and those with electron-donating substituents (Y = $OCH_3$ and $CH_3$) were good substrates for the oxidation reaction with palladium nitrate. Thus, the reaction mechanism of the oxygen transfer was proposed to include nucleophilic benzylic carbon.

• Journal of the Korean Chemical Society
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• v.26 no.5
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• pp.340-348
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• 1982

The presence of 10 mole percent triphenyl borate accelerated dramatically the rate of reduction of structurally different sulfoxides with borane in tetrahydrofuran at room temperature, compared to the slow reduction with borane itself. Tetramethylene sulfoxide underwent complete reduction in 5 min and diethyl sulfoxide, dibenzyl sulfoxide and benzylphenyl sulfoxide were reduced quantitatively within 1h, whereas the reduction of diphenyl sulfoxide was rather slow, giving diphenyl sulfide in 90% yield in 24h. Boron trifluoride etherate and triethyl borate were less effective than triphenyl borate. A possible mechanism is presented.